Iodoethane → L-Leucine ethyl ester

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% dispersion in oil: 4.5 g, 0.11 mol) was added to a stirred solution of L-leucinol (12.8 ml, 0.10 mol) in a mixture of dry acetonitrile (24 ml) and dry THF (200 ml) at room temperature under argon. The mixture was heated at reflux for 2 h, cooled to 55° C. and ethyl iodide (8.2 ml, 0.10 mol) added carefully. The reaction mixture was heated at reflux overnight and allowed to cool to room temperature. Ice cold brine (100 ml) was added carefully and the mixture extracted with ethyl acetate (3×100 ml). The combined organic extracts were dried over anhydrous sodium sulphate, filtered and evaporated. The residue was distilled under reduced pressure to give L-leucinyl ethyl ether (4.5 g, 30%) as a colourless oil which was used directly in the next step.

Provenance & Evidence